Chiral Enantioselective Assemblies Induced from Achiral Porphyrin by l- and d-Lysine.

Abstract

π-Conjugated porphyrins have aroused particular attention for nanofabrication and biomimics; however, little attention has been paid to porphyrins-based chiral analysis owing to the achiral feature of porphyrins. Here, we demonstrated a chiral self-assembly of achiral porphyrin induced by l- and d-lysine (l- and d-Lys), and the resultant porphyrin self-assembly exhibited alterable morphologies depending on the inducer used (l- or d-Lys). The supramolecular chirality of the self-assembly was characterized by circular dichroism (CD) spectra, confirming successful transfer of molecular chirality from l- and d-Lys to the self-assembly. The enantioselective property of the chiral self-assembly was also investigated by using tryptophan (Trp) isomers as the model, and the results indicated that the developed chiral self-assembly showed significantly higher affinity toward l-Trp than d-Trp. Also in this work, the l-/d-Lys-induced chiral self-assembly of porphyrin and the supramolecular interaction between the self-assembly and l-/d-Trp were also studied by density functional theory (DFT).